• Archives of Pharmacal Research
• /
• 제23권4호
• /
• pp.315-323
• /
• 2000

Syntheses of new analogues of oxathiin carboxanilide (UC84) and their antiviral activities were described. The heterocyclic carboxylic acids including oxathiins (4), thiazines (9) and dithiins (13) in which the methyl was replaced either by lipophilic trifluoromethyl- or bulky phenylgroup were synthesized starting from $\beta$-keto esters (5). Reaction of 4, 9 and 13 with thionyl chloride followed by treatment of the substituted aniline 22 gave the corresponding carboxanilides (24a~24f). The carboxanilides were subjected to Laweson's reagent the corresponding thiocarboxanilides (24g~24k). The antiviral activities of the synthesized compounds against human immunodeficiency virus type 1 (HIV-1), poliovirus type 1 (PV-1 ), coxsackie B virus type 3 (CoxB-3), vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1) were presented. The antiviral activity against HIV-1 of dithiin carboxanilide (24e) was similar with that of UC84 (24a). The corresponding thiocarboxanilides (24g~24k) showed higher inhibitory activity against HIV-1 than the carboxanilides (24a, 24b, 24d, 24e). The compounds in which ether the lipophilic trifluorormethyl substituents (24d, 24f, 24i ,24k) or bulky phenyl substituent is present in the heterocyclic compounds showed lower inhibitory activity than that of the methyl substituents is present in the compounds against the HIV-1. But the trifluoromethylated dithiin (24f) showed higher inhibitory activity against PV-1 and CoxB-3 virus than commercial antiviral agents, ribavirin (RV).

• 한국작물학회지
• /
• 제42권6호
• /
• pp.821-832
• /
• 1997

본 실험은 알파파 꽃 추출물로부터 Allelopathy와 Autotoxicity에 관련되는 활성물질을 분리, 동정하기 위하여 실시하였다. 알팔파 꽃 200g을 80% MeOH로 추출하여 $CHCl_3$층을 silica gel thin layer chromatography (TLC), microcrystalline cellulose thin layer chromatography (MCTLC)와 droplet countercurrent chromatography(DCCC)의 분획을 이용하여 생물검정을 행하고 DCCC의 생물검정에서 가장 억제력을 보였던 분획 5와 6은 HPLC로 활성물질을 동정하였다. HPLC분석 결과 분획 5에서는 ferulic acid, caffeic acid, vanillic acid, rutin, narringin 이, 분획 6에서는 ferulic acid, caffeic acid, vanillic acid, rutin, coumarin이 동정되었다. 이들 동정된 물질을 이용한 알팔파와 돌피에 대한 발아실험에서도 모두 알팔파와 돌피의 발아와 생육에 억제적으로 작용하였으며, 이중 coumarin의 처리가 가장 억제적이었다. 따라서 이들 물질이 알팔파와 돌피의 autotoxicity와 allelopathy에 관련하는 것으로 생각되었다.

• Natural Product Sciences
• /
• 제22권2호
• /
• pp.111-116
• /
• 2016

Phytochemical investigation of the stems of Pueraria lobata (Wild) Ohwi (Leguminosae), led to the isolation of eighteen known compounds: ${\beta}$-amyrone (1), (+)-pinoresinol (2), (+)-syringaresinol (3) $(+)-syringaresinol-O-{\beta}-{\small{D}}-glucoside$ (4), (+)-lariciresinol (5), (-)-tuberosin (6), naringenin (7), liquiritigenin (8), isoliquiritigenin (9) genistein (10), daidzein (11) daidzin (12) daidzein 4',7-diglucoside (13) 2,4,4'-trihydroxy deoxybenzoin (14), S-(+)-1-hydroxy-3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxy-phenyl)propan-2-one (15), methyl $2-O-{\beta}-{\small{D}}-glucopyranosylbenzoate$ (16), pyromeconic acid $3-O-{\beta}-{\small{D}}-glucopyranoside$ 6'- (O-4''-hydroxy-3-methoxybenzoate) (17), and allantion (18). The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of those data with previously published results. The effects of isolated compounds on mushroom tyrosinase enzymatic activity were screened. The results indicated that, chloroform extract of P. lobata stems turned out to be having tyrosinase inhibitory effect, and only compounds 5, 8, 9, and 11 showed enzyme inhibitory activity, with $IC_{50}$ values of $21.49{\pm}4.44$, $25.24{\pm}6.79$, $4.85{\pm}2.29$, and $17.50{\pm}1.29{\mu}M$, respectively, in comparison with these of positive control, kojic acid ($IC_{50}\;12.28{\pm}2.72{\mu}M$). The results suggest that P. lobata stems extract as well as its chemical components may represent as potential candidates for tyrosinase inhibitors.

• Mycobiology
• /
• 제47권2호
• /
• pp.256-260
• /
• 2019

Neuraminidase (NA) cleaves the glycosidic bond linkages of sialic acids to release the mature virions from infected cells and has been an attractive therapeutic target for anti-influenza agents. In our ongoing investigation of NA inhibitors in mushroom extracts, we found that the extract the fruiting body of Glaziella splendens potently inhibited neuraminidase. The fruiting bodies of G. splendens were extracted and partitioned successively with hexane, ethyl acetate, and butanol. The ethyl acetate soluble-layer was subjected to silica gel and Sephadex LH-20 column chromatographies, and MPLC to obtain five compounds (1-5). Their structures were determined by spectroscopic methods. NA inhibitory activity of these compounds was evaluated using NAs from recombinant rvH1N1, H3N2, and H5N1 influenza A viruses. One compound (1) was elucidated as a new azaphilone derivative, and four compounds (2-5) were identified as entonaemin A, comazaphilone D, rubiginosin A, and entonaemin B, respectively. Compounds 3 and 4 showed considerable inhibitory activity against three types of neuraminidases with the $IC_{50}$ values of 30.9, 41.8, and $35.7{\mu}M$ for 3 and 46.5, 50.4, and $29.9{\mu}M$ for 4, respectively. This study reveals that the fruiting bodies of G. splendens possess azaphilone derivatives with the NA inhibitory activity. This is the first report on the isolation of neuraminidase inhibitors from the fruiting bodies of G. splendens.

• 한국자원식물학회지
• /
• 제11권
• /
• pp.89-109
• /
• 1998

Screening of new antioxidants form oriental medicines resulted in the isolation of a new antioxidative compound and eight known compounds from the stem bark of Kalopanax pictus. On the basis of various spectrosopic studies, the structure of the new compound was determined to be 4-rhamnose-3,5-dimethoxybenzoic acid methly ester. Other known compounds were identified as ferulic acid, 4,5,6,-trihydroxyflavanone, 2', 4',4' -trihydroxychalcone, caffeic acid, coniferyl alcohol, syringin, 1,3-di-O-caffeoylquinic acid. These compounds showed lipid peroxidation inhibitory acitivity in rat liver microsomes and free radical scavenging acitivity.

• Biomolecules & Therapeutics
• /
• 제31권1호
• /
• pp.108-115
• /
• 2023

Numerous psychotropic and addictive substances possess structural features similar to those of β-phenethylamine (β-PEA). In this study, we selected 29 β-PEA derivatives and determined their structure-activity relationship (SAR) to their ability to inhibit dopamine (DA) reuptake; conducted docking simulation for two selected compounds; and identified their potential functionals. The compounds were subdivided into arylethylamines, 2-(alkyl amino)-1-arylalkan-1-one derivatives and alkyl 2-phenyl-2-(piperidin-2-yl)acetate derivatives. An aromatic group, alkyl group, and alkylamine derivative were attached to the arylethylamine and 2-(alkyl amino)-1-arylalkan-1-one derivatives. The inhibitory effect of the compounds on dopamine reuptake increased in the order of the compounds substituted with phenyl, thiophenyl, and substituted phenyl groups in the aromatic position; compounds with longer alkyl groups and smaller ring-sized compounds at the alkylamine position showed stronger inhibitory activities. Docking simulation conducted for two compounds, 9 and 28, showed that the (S)-form of compound 9 was more stable than the (R)-form, with a good fit into the binding site covered by helices 1, 3, and 6 of human dopamine transporter (hDAT). In contrast, the (R, S)-configuration of compound 28 was more stable than that of other isomers and was firmly placed in the binding pocket of DAT bound to DA. DA-induced endocytosis of dopamine D₂ receptors was inhibited when they were co-expressed with DAT, which lowered extracellular DA levels, and uninhibited when they were pretreated with compound 9 or 28. In summary, this study revealed critical structural features responsible for the inhibition of DA reuptake and the functional role of DA reuptake inhibitors in regulating D₂ receptor function.

• 한국식품저장유통학회지
• /
• 제25권1호
• /
• pp.117-123
• /
• 2018

이팝나무 꽃으로부터 phenolic 화합물을 추출하기 위하여 열수와 90% 에탄올로 phenolic compounds를 추출하였다. Xanthine oxidase 저해 효과를 측정한 결과, 열수와 에탄올 추출물 $200{\mu}g/mL$ phenolics 농도에서 각각 25.60, 15.92%의 저해 효과를 나타내었다. ${\alpha}$-Glucosidase 저해 효과를 측정한 결과 $200{\mu}g/mL$ phenolics 농도의 에탄올 추출물에서 100.00%의 매우 높은 저해 효과를 나타내었다. 미백효과를 측정하는 tyrosinase 저해 효과를 측정한 결과, 열수와 에탄올 추출물 $200{\mu}g/mL$ phenolics 농도에서 각각 17.27, 36.13%의 저해 효과를 나타내었다. 주름개선 효과를 측정하는 collagenase, elastase 저해 효과를 측정한 결과 에탄올 추출물에서는 $200{\mu}g/mL$ phenolics 농도에서 각각 96.26, 35.93%의 저해 효과를 나타내었다. 항염증 효과를 측정하는 hyaluronidase 저해 효과를 측정한 결과, 열수와 에탄올 추출물 $200{\mu}g/mL$ phenolics 농도에서 각각 36.96, 88.70%의 저해 효과를 나타내었다. 따라서 이팝나무 꽃에서 분리된 phenolic compounds는 $50-200{\mu}g/mL$ phenolics 농도 범위에서 항통풍, 당분해 억제, 미백, 주름개선 및 항염증과 관련된 생리활성 효소를 농도 의존적으로 유의하게 저해하는 것을 확인하였고, 이를 이용한 건강기능성 식품 및 미용식품의 기능성 소재로 활용 가능하다고 판단되었다.

• 생약학회지
• /
• 제34권1호통권132호
• /
• pp.86-90
• /
• 2003

For the determination of inhibiting cytochrome P450(CYP)3A4 activity, an improvement HPLC method was established by using a new internal standard and solvent system. Moreover, CYP3A4 amount for a optimum reaction of enzyme was determined by a comparative study with a variety concentration of enzyme. Using a established method, inhibitory effect of CYP3A4 that is drug metabolizing enzyme Investigated on EtOAc extracts of 5-class spices. As a result of experiment, EtOAc extract of white pepper (Piper nigrum L.) showed strong inhibitory activity. On a continuous experiment, the fraction 2, 4 and 5 of while pepper extract showed remarkable inhibitory activity. Pipeline, a main constituent of pepper was not included in these fraction. It is suggested that major compounds for the inhibitory activity of white pepper may be other ingredient that is not piperine.

• 분석과학
• /
• 제7권3호
• /
• pp.403-411
• /
• 1994

본 실험은 알팔파의 Allelopathy와 Autotoxicity에 관련되는 생리활성 물질의 분리, 정제, 동정하기 위하여 실시되었다. 알팔파 생잎 1kg을 80% MeOH로 추출하여 silica gel TLC와 DCCC의 분리와 정제과정을 거쳐 HPLC로 동정하였다. HLPC 분석결과 4개의 phenolic 물질(salicylic acid, rutin, quercetin, scopoletin) 등이 동정되었다. 이들 물질을 이용한 발아실험에서도 모두 알팔파의 발아와 생육에 억제적으로 작용하였으며, 이 중 quercetin의 처리가 가장 억제적이었다. 따라서 최소한 이들 물질이 알팔파의 Allelopathy와 Autotoxicity에 관련하는 것으로 생각되었다.

• Natural Product Sciences
• /
• 제21권1호
• /
• pp.6-13
• /
• 2015

Phytochemical investigation of the aerial components of Ducrosia ismaelis Asch. led to the isolation of six known compounds, psoralen (1), isopsoralen (2), cnidioside A (3), (-)-syringaresinol-O-${\beta}$-D-glucopyranoside (4), (E)-plicatin B (5), trilinolein (6). The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of these data with previously published results. The antioxidant, anti-osteoporotic and cardiovascular related activities of the isolated compounds were assessed using oxygen radical absorbance capacity (ORAC), reducing capacity, tartrate-resistant acid phosphatase (TRAP), and soluble epoxide hydrolase (sEH) inhibitory activity assays. Compounds (3-5) showed potent peroxyl radical-scavenging capacities with ORAC values of $11.06{\pm}0.39$, $7.98{\pm}0.10$, and $13.99{\pm}0.06$ Trolox equivalent (TE) at concentrations of $10{\mu}M$, respectively. Only compounds 4 and 5 was able to significantly reduce $Cu^{2+}$ ions, with a reduction value of $9.06{\pm}0.32$ and $4.61{\pm}0.00{\mu}M$ Trolox Equivalent (TE) at a concentration of $10{\mu}M$. Compound 5 at $10{\mu}M$ exhibited a potent inhibitory effect on osteoclastic TRAP activity with a TRAP value of $86.05{\pm}6.55%$ of the control. Compounds 1, 3 and 5 potently inhibited sEH activity with $IC_{50}$ values of 41.6 4.9, 16.0 1.1, and 49.0 $5.7{\mu}M$, respectively.